Title: 20 Best B&B in Winchester, VA - Bed and Breakfast from $158 | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx6056879)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.com/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d6056879.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-05-15&endDate=2026-05-17&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester bed & breakfast ![Exterior](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/6e95af26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/e1bc7cf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/480b5c82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/df92df6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glen Gordon Manor [](https://www.expedia.com/Huntly-Hotels-Glen-Gordon-Manor.h19126061.Hotel-Information) Huntly 9.8/10 Exceptional (96 reviews) "Staff was efficient, professional, personable, thoughtful. Facilities were lovely, Breakfast was excellent." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander and Judith $299 nightly $327 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/Huntly-Hotels-Glen-Gordon-Manor.h19126061.Hotel-Information) ![Garden view](https://images.trvl-media.com/lodging/37000000/36140000/36132200/36132129/f6325d64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily local cuisine breakfast](https://images.trvl-media.com/lodging/37000000/36140000/36132200/36132129/098eec3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/37000000/36140000/36132200/36132129/2db74ae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/37000000/36140000/36132200/36132129/2c3deef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Loudoun Valley Manor [](https://www.expedia.com/Waterford-Hotels-Loudoun-Valley-Manor.h36132129.Hotel-Information) Waterford 9.6/10 Exceptional (283 reviews) "Beatiful Location Reasonable Rates Great Breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Albert $138 nightly $158 total Mar 19 - Mar 20 Total with taxes and fees [](https://www.expedia.com/Waterford-Hotels-Loudoun-Valley-Manor.h36132129.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/7b9d69e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/80e06b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (The Overlook) | Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/8ab65f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/f0afdbe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hillbrook Inn [](https://www.expedia.com/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information) Charles Town 8.6/10 Excellent (676 reviews) "Wonderful staff, and fall cottage was lovely." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Henrik $170 nightly $188 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/17000000/16290000/16281800/16281705/f4cdce70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 King Bed, Hot Tub, Garden View | 1 bedroom, premium bedding, pillowtop beds, iron/ironing board](https://images.trvl-media.com/lodging/17000000/16290000/16281800/16281705/686105c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/17000000/16290000/16281800/16281705/170acaf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/17000000/16290000/16281800/16281705/827ae686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stone Manor Boutique Inn [](https://www.expedia.com/Lovettsville-Hotels-Stone-Manor-Boutique-Inn.h16281705.Hotel-Information) Lovettsville 9.6/10 Exceptional (97 reviews) "The breakfast was fabulous and the room great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MICHEL $230 nightly $262 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Lovettsville-Hotels-Stone-Manor-Boutique-Inn.h16281705.Hotel-Information) ![Hallway](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/8659900e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/0932b9ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/w1568h1045x16y15-fb28d00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/3be58fba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Evergreen [](https://www.expedia.com/Haymarket-Hotels-Inn-At-Evergreen.h15733502.Hotel-Information) Haymarket 9.4/10 Exceptional (133 reviews) "Beautiful property and excellent food." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paula $254 nightly $290 total Mar 20 - Mar 21 Total with taxes and fees [](https://www.expedia.com/Haymarket-Hotels-Inn-At-Evergreen.h15733502.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/19000000/18670000/18669500/18669467/a14a8657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18670000/18669500/18669467/3abc3b5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living room](https://images.trvl-media.com/lodging/19000000/18670000/18669500/18669467/f7ffda1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/19000000/18670000/18669500/18669467/4272811e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cantuta Inn [](https://www.expedia.com/Martinsburg-Hotels-Cantuta-Inn.h18669467.Hotel-Information) Harpers Ferry 9.0/10 Wonderful (76 reviews) "The hostess and her husband were friendly and made us feel very welcome! Breakfast was scrambled eggs with fruit and was nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ron $165 nightly $185 total Mar 24 - Mar 25 Total with taxes and fees [](https://www.expedia.com/Martinsburg-Hotels-Cantuta-Inn.h18669467.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/118000000/117730000/117723700/117723633/7918f369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/118000000/117730000/117723700/117723633/8d2e7c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/118000000/117730000/117723700/117723633/2f491ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117730000/117723700/117723633/4ee27c5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Grass Roots Hill [](https://www.expedia.com/Purcellville-Hotels-The-Inn-At-Grass-Roots-Hill.h117723633.Hotel-Information) Purcellville 9.4/10 Exceptional (8 reviews) "House and property are absolutely beautiful. Staff are amazing and super friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chad $459 nightly $523 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Purcellville-Hotels-The-Inn-At-Grass-Roots-Hill.h117723633.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34100000/34090700/34090623/ff8b2dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/35000000/34100000/34090700/34090623/02c49060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34100000/34090700/34090623/e770d74d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34100000/34090700/34090623/1f81d6e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Van Gogh Room in Villa [](https://www.expedia.com/Purcellville-Hotels-The-Van-Gogh-Room-In-Villa.h34090623.Hotel-Information) Purcellville 9.0/10 Wonderful (67 reviews) "Quiet setting and friendly owner." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Helen W. $337 nightly $384 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Purcellville-Hotels-The-Van-Gogh-Room-In-Villa.h34090623.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/a8e8b9f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Queen Bed, Balcony | Balcony](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/f1d7b990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/e996c5c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/3b25e32e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hopkins Ordinary Bed Breakfast and Ale Works [](https://www.expedia.com/Sperryville-Hotels-Hopkins-Ordinary-Bed-Breakfast-And-Ale-Works.h27137088.Hotel-Information) Sperryville 9.8/10 Exceptional (32 reviews) "Great place. Good food, great beer." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phil $279 nightly $305 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Sperryville-Hotels-Hopkins-Ordinary-Bed-Breakfast-And-Ale-Works.h27137088.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34330000/34329600/34329573/78704f31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34330000/34329600/34329573/aafbdad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34330000/34329600/34329573/e0f66792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34330000/34329600/34329573/957e6eda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view. [](https://www.expedia.com/Purcellville-Hotels-Monet-HoneymoonSuite-Elegant-Lrg-2rm-Wbalcony-In-VillaMountnpasture-Pool-View.h34329573.Hotel-Information) Purcellville 9.8/10 Exceptional (37 reviews) "Beautiful location, quiet, and Maud is a wonderful person." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis G. $421 nightly $480 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Purcellville-Hotels-Monet-HoneymoonSuite-Elegant-Lrg-2rm-Wbalcony-In-VillaMountnpasture-Pool-View.h34329573.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/8458539f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/390101c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/1a36bdf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/9df5645f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gay Street Inn [](https://www.expedia.com/Washington-Hotels-Gay-Street-Inn.h26679788.Hotel-Information) Washington 10/10 Exceptional (34 reviews) "Beautiful historic Inn with incredible owners and service. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee $359 nightly $387 total Mar 19 - Mar 20 Total with taxes and fees [](https://www.expedia.com/Washington-Hotels-Gay-Street-Inn.h26679788.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186918/03c5456b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186918/acb4aae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186918/98345320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186918/e3ef8a74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B [](https://www.expedia.com/Berkeley-Springs-Hotels-Bird-Nest-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186918.Hotel-Information) Berkeley Springs 10/10 Exceptional (3 reviews) "Beautiful house. Renovations are not quite complete yet, and the electronic locks needed extra communication with the owner to use, but still a great stay. Perfect location and this place will be gorgeous after renovations are complete." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel F. $266 nightly $295 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Berkeley-Springs-Hotels-Bird-Nest-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186918.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/30ef090b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Sunrise Room | Individually decorated, individually furnished, blackout drapes](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/7a2a968f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/6f99e56e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/52d84062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Carriage Inn B&B [](https://www.expedia.com/Martinsburg-Hotels-The-Carriage-Inn-BB.h2762649.Hotel-Information) Charles Town 9.6/10 Exceptional (442 reviews) "Excellent accommodations and breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William $157 nightly $178 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Martinsburg-Hotels-The-Carriage-Inn-BB.h2762649.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/36000000/35230000/35223100/35223045/57d635cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boudoir King Suite | In-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/36000000/35230000/35223100/35223045/ccee4579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/36000000/35230000/35223100/35223045/c12f5cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/36000000/35230000/35223100/35223045/91a21401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn of the Shenandoah [](https://www.expedia.com/Luray-Hotels-Inn-Of-The-Shenandoah.h35223045.Hotel-Information) Luray 9.8/10 Exceptional (40 reviews) "It was an awesome place to stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eileen $303 nightly $364 total Mar 24 - Mar 25 Total with taxes and fees [](https://www.expedia.com/Luray-Hotels-Inn-Of-The-Shenandoah.h35223045.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186922/e5fc9b79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186922/fdd8e807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186922/15a3d4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video library](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186922/bcee6e6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B [](https://www.expedia.com/Berkeley-Springs-Hotels-Appalachian-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186922.Hotel-Information) Berkeley Springs 10/10 Exceptional (3 reviews) "My partner and I have both stayed in some pretty high end hotels and we were so impressed!! By far the best VRBO i’ve stayed in-newly renovated and decorated. You don’t want to pass up this hidden gem convenient to everything in Berkeley Springs!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deirdre A. $279 nightly $310 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Berkeley-Springs-Hotels-Appalachian-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186922.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186920/6f6e84c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186920/b98f28d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186920/a606ba47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video library](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186920/7c9f1c3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Appalachian Suite In Town!- The Grand Castalian Inn B&B [](https://www.expedia.com/Berkeley-Springs-Hotels-Appalachian-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186920.Hotel-Information) Berkeley Springs 10/10 Exceptional (2 reviews) "We loved the spot and will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Seth W. $279 nightly $310 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Berkeley-Springs-Hotels-Appalachian-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186920.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108020000/108011600/108011538/9485d69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108020000/108011600/108011538/bafd7590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108020000/108011600/108011538/4db9e83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108020000/108011600/108011538/b4a25399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 50's Drive-In Inside the Grand Castalian Inn B&B [](https://www.expedia.com/Berkeley-Springs-Hotels-50s-Drive-In-Inside-The-Grand-Castalian-Inn-BB.h108011538.Hotel-Information) Berkeley Springs $292 nightly $324 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Berkeley-Springs-Hotels-50s-Drive-In-Inside-The-Grand-Castalian-Inn-BB.h108011538.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-30&endDate=2026-03-31®ionId=6056879&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d6056879-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d6056879-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/c93a366a_y.jpg) ### SpringHill Suites by Marriott Winchester 10/10 Excellent "SpringHill Suites is my go-to hotel in the Winchester area. " [](https://expedia.com/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Quality Inn Harpers Ferry - Charles Town](https://images.trvl-media.com/lodging/1000000/30000/25200/25179/e301290f_y.jpg) ### Quality Inn Harpers Ferry - Charles Town 10/10 Excellent "Clean room in good shape, temperature great, close to park, breakfast very good. All staff very pleasant!" [](https://expedia.com/Martinsburg-Hotels-Quality-Inn.h25179.Hotel-Information) ![Sleep Inn & Suites Winchester near University](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/554af346_y.jpg) ### Sleep Inn & Suites Winchester near University 2/10 Terrible "This is the dirtiest hotel I’ve ever stayed at. There was an earwig in the bathroom. The bed cover was dirty, everything was dingy. The walls, the chair. The one side of the mattress springs were so wore and broken. The plug in the bathroom didn’t work. The handicap bar was out of the wall. You can hear the people upstairs walking around. Luckily, the sheets themselves were clean and didn’t smell. Wasn’t worth my 8 hour stay to bother moving rooms. Water was extremely hot! " [](https://expedia.com/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) ![Holiday Inn Express Charles Town by IHG](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/d75699e6_y.jpg) ### Holiday Inn Express Charles Town by IHG 10/10 Excellent "Didn’t use either. Breakfast was great" [](https://expedia.com/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.Hotel-Information) ![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/c10d527c_y.jpg) ### Hampton Inn Winchester-University/Mall Area 10/10 Excellent "Nice lobby, nice room, ample parking, good breakfast selection, good area around the hotel" [](https://expedia.com/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "Great stay!" [](https://expedia.com/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/9e66afda_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "Not your average hotel. Unique room layout, modern lobby and friendly staff! " [](https://expedia.com/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Hampton Inn Martinsburg](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/c1c4db32_y.jpg) ### Hampton Inn Martinsburg 10/10 Excellent "Staff was extremely friendly and helpful! Loved the welcoming message from the front desk. Would definitely stay again!" [](https://expedia.com/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.Hotel-Information) ![Courtyard by Marriott Winchester](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/1b2ad59b_y.jpg) ### Courtyard by Marriott Winchester 10/10 Excellent "Great location" [](https://expedia.com/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 1,963 | | ----------------- | ------ | | Accommodation | 34 B&B | | Lowest Price | $158 | | Highest Price | $523 | ## Frequently asked questions ### What is the nightly rate for a Bed and Breakfast in Winchester? ### When is the best time to book a Bed and Breakfast in Winchester? > September often sees a delightful mix of warm days and cool evenings, making it ideal for leisurely strolls through local parks or visiting historical sites. The community also hosts several festivals celebrating the harvest, offering visitors a taste of local culture and cuisine. > > > For those seeking a more budget-friendly experience, consider planning your trip in November. This quieter month provides a unique opportunity to explore Winchester's attractions without the crowds, and you can enjoy the area's natural beauty as the landscape transitions into winter. ### What is the difference between a Winchester Bed & Breakfast and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Hotels near Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels) - [Historic Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Historic-Hotel.0-n6164092-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Restaurants in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Restaurants.0-n6164092-0-tHotelswithRestaurants.Travel-Guide-Filter-Hotels) - [Casino Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Casino-Hotel.0-n6164092-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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[Bright Box Theater ](https://www.expedia.com/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Vacation-Attraction) - [Shenandoah Valley Discovery Museum ](https://www.expedia.com/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Vacation-Attraction) - [George Washington's Office ](https://www.expedia.com/George-Washingtons-Office-Old-Town-Winchester.d6164042.Vacation-Attraction) - [Mt Hebron Cemetery ](https://www.expedia.com/Mt-Hebron-Cemetery-Winchester.d553248621532661845.Vacation-Attraction) - [Patsy Cline Historic House ](https://www.expedia.com/Patsy-Cline-Historic-House-Winchester.d553248621532661841.Vacation-Attraction) - [Museum of the Shenandoah Valley ](https://www.expedia.com/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction) - [Jim Barnett Park ](https://www.expedia.com/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Abram's Delight ](https://www.expedia.com/Abrams-Delight-Winchester.d553248621532661839.Vacation-Attraction) - [Nalls Farm Market ](https://www.expedia.com/Nalls-Farm-Market-Winchester.d553248621532661846.Vacation-Attraction) - [Shenandoah University ](https://www.expedia.com/Shenandoah-University-Winchester.d6127311.Vacation-Attraction) - [Rock Harbor Golf Course ](https://www.expedia.com/Rock-Harbor-Golf-Course-Winchester.d553248621561864838.Vacation-Attraction) - [Car rentals near Old Town Winchester ](https://www.expedia.com/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide) - [Car rentals near Patsy Cline Historic House ](https://www.expedia.com/Car-Rentals-In-Patsy-Cline-Historic-House.d553248621532661841.Car-Rental-Guide) - [Car rentals near Nalls Farm Market ](https://www.expedia.com/Car-Rentals-In-Nalls-Farm-Market.d553248621532661846.Car-Rental-Guide) - [Car rentals near Shenandoah University ](https://www.expedia.com/Car-Rentals-In-Shenandoah-University.d6127311.Car-Rental-Guide) - [Van Car Rentals near Shenandoah University ](https://www.expedia.com/Van-Car-Rentals-In-Shenandoah-University.d6127311-tVan.Car-Rental-Guide-Class) - 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